4-chloromethyl-2-[(E)-styryl]thiazole → 4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-[(E)-2-phenylethenyl]thiazole

HRID 322384Notes

Reaction equation

HRID 322384 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:4][CH:3]=1.Cl[CH2:17][C:18]1[N:19]=[C:20](/[CH:23]=[CH:24]/[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[S:21][CH:22]=1>>[N:11]1([CH2:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([O:1][CH2:17][C:18]3[N:19]=[C:20](/[CH:23]=[CH:24]/[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[S:21][CH:22]=3)=[CH:3][CH:4]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

3

Reactant 2

HCID 220097354-chloromethyl-2-[(E)-styryl]thiazoleHCID 220098181-[3-(4-Hydroxyphenyl)propyl]imidazole

Product 1

HCID 220098444-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-[(E)-2-phenylethenyl]thiazoleYield 58%

Procedure

In substantially the same manner as in Working Example 48, 1-[3-(4-hydroxyphenyl)propyl]imidazole was allowed to react with 4-chloromethyl-2-[(E)-2-phenylethenyl]thiazole to give 4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-[(E)-2-phenylethenyl]thiazole. The yield was 58%. Recrystallization from ethyl acetate gave colorless prisms, mp 129-130° C.

Sources & evidence

ORD record
ord-1508c70e71b04be593bc1bdc36a85574
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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